- MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides
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A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.
- Rahmatpour, Ali,Zamani, Maryam
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- Efficient and regioselective ring-opening of epoxides with alcohols and sodium azide by using catalytic amounts of gacl3/polyvinylpyrrolidone
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A new polymeric catalyst was prepared by supporting GaCl3 on cross-linked polyvinylpyrrolidone (GaCl3/ PVP). This catalyst was employed for efficient and regioselective ring-opening reaction of epoxides by various alcohols under solvent-free conditions at room temperature. In our procedure, this heterogeneous catalyst was used at neutral and mild reaction conditions to afford high yields of β-alkoxy alcohols. Also, regioselective conversion of epoxides to β-azidohydrines was accomplished by sodium azide in MeOH in the presence of GaCl3/PVP at room temperature. GaCl3/PVP is a non-hygroscopic and recoverable catalyst and is easily separated from reaction mixture by a simple filtration and re-used repeatedly. Also, this catalyst has good handling and can be stored for long time without any reducing of its reactivity.
- Pourali, Ali Reza,Ghayeni, Samaneh,Afghahi, Fatemeh
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p. 1741 - 1744
(2013/07/26)
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- Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)
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Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.
- Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Yadollahi, Bahram,Mirmohammadi, S. Mohammad R.
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p. 235 - 242
(2007/10/03)
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- Reaction of 1-amino-3-propoxy-2-propanol with aldehydes
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The reaction of 1-amino-3-propoxy-2-propanol was examined as a route to the corresponding 1,3-oxazolidines.
- Badalova,Mamedova,Alieva,Magerramov,Allakhverdiev
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p. 1656 - 1658
(2007/10/03)
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- Synthesis of 1-alkoxy-3-N-succinimido-2-propanols
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Procedures for preparing 1-alkoxy-3-chloro-2-propanols, with their subsequent transformation to 1-alkoxy-N-succinimido-2-propanols, were developed.
- Gasanov,Allakhverdiev
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p. 2026 - 2028
(2007/10/03)
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- Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin
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The new electron deficient tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(tpp)(OTf)2], was used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides. Conversion of epoxides to thiiranes and acetonides were also performed efficiently in the presence of this catalyst.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Shaibani, Reza
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p. 6105 - 6111
(2007/10/03)
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- Silica sulfuric acid; an efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of silica sulfuric acid with high degree of regioselectivity. The catalyst is reusable and can be applied several times without any decrease in the yield of reactions.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Fard, Mohammad Ali Bodaghi
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p. 1113 - 1121
(2007/10/03)
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- Efficient regio- and stereoselective ring opening of epoxides with alcohols, acetic acid and water catalyzed by ammonium decatungstocerate(IV)
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Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, ([CeW10O36] 8-), affording the corresponding β-alkoxy and β-acetoxy alcohols in high yields. In water, ring opening of epoxides occurs with this catalyst to produce the corresponding diols in good yields.
- Mirkhani, Valiollah,Tangestaninejad, Shahram,Yadollahi, Bahram,Alipanah, Ladan
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p. 8213 - 8218
(2007/10/03)
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- Magnesium hydrogensulfate: A cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO4)2, with high degree of regioselectivity. The reactions are chemoselective and many of the other functional groups such as ethereal carbon oxygen bonds as well as carbon-carbon double bond remain intact under the reaction conditions. Epoxides also react with thiourea or ammonium thiocyanate in the presence of Mg(HSO 4)2 to afford the corresponding thiiranes in good to excellent yields.
- Salehi, Peyman,Khodaei, Mohammad Mahdi,Zolfigol, Mohammad Ali,Keyvan, Afsaneh
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p. 3041 - 3048
(2007/10/03)
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- Iron perchlorate on silica gel as multi-purpose reagent for catalysis of closure and rupture of carbon-oxygen bond in epoxides, alcohols, and esters
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Aliphatic alcohols and water in the presence of catalytic amounts of Fe3+ ion introduced as iron(III) perchlorate on silica gel carrier perform efficient regiospecific opening of an epoxy ring. Carbon acids esterification with various type alcohols was carried out using the system Fe(ClO4)3-silica gel in dichloromethane under conditions excluding solvolysis. Acetylation and formylation of alcohols was performed by efficient transesterification with ethyl acetate and ethyl formate.
- Salechi,Khodaei,Ghareghani,Motlagh
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p. 794 - 796
(2007/10/03)
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- Ferric perchlorate: An efficient reagent for regio- and stereoselective alcoholysis and hydrolysis of epoxides
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Regio- and stereoselective ring opening reaction of epoxides is achieved efficiently by aliphatic alcohols and water in the presence of catalytic amounts of ferric perchlorate.
- Salehi, Peyman,Seddighi, Behnam,Irandoost, Mohsen,Kargar Behbahani, Farahnaz
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p. 2967 - 2973
(2007/10/03)
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- Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides
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Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.
- Iranpoor, Nasser,Adibi, Hadi
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p. 675 - 680
(2007/10/03)
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- Bismuth(III) chloride (BiCl3); an efficient catalyst for mild, regio- and stereoselective cleavage of epoxides with alcohols, acetic acid and water
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Epoxides can be cleaved in a regio- and stereoselective manner with alcohols, acetic acid and water in the presence of catalytic amounts of bismuth(III) chloride, affording the corresponding β-alkoxy and β-acetoxy alcohols and diols in high yields.
- Mohammadpoor-Baltork,Tangestaninejad,Aliyan,Mirkhani
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p. 2365 - 2374
(2007/10/03)
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- The kinetics of chloromethyloxirane reaction with alcohols and their adducts in the presence of stannic chloride
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Rate constants of the reaction of chloromethyloxirane (epichlorohydrin) with methyl, n-propyl, isopropyl, n-, sec-, tert-butyl, n-hexyl, n-octyl, and n-decyl alcohols in the presence of stannic chloride were studied at 30, 40, and 50°C. Reaction is not first order in respect to epichlorohydrine and is particularly fast at the beginning and its rate constants are proportional to the concentration of the catalyst. The rate constants increase in the homologous series of C1-C10 alcohols. The reaction rates of 2-chloromethyloxirane with 1-chloromethyl-2-alkoxyethanols are ca. 2.5-times larger than that with corresponding alcohols.
- Chlebicki,Pozniak
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- Highly efficient, regio- and stereoselective ring opening of epoxides and thiiranes with Ce(OTf)4
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Ceric triflate, Ce(OTf)4 is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation to the corresponding disulfides occur efficiently in the presence of this reagent. A mild method for the preparation of dithianes from thiiranes and Ce(OTf)4 is also described.
- Iranpoor,Shekarriz,Shiriny
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p. 347 - 366
(2007/10/03)
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- Electrogenerated Acid as an Efficient Catalyst for Alcoholyses and Hydrolyses of Epoxides
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The electrochemical transformation of different epoxides to their corresponding β-alkoxy alcohols and diols was achieved by using an electrogenerated acid-catalyst.A competitive ring-opening reaction of activated epoxides in the presence of deactivated epoxides was also successfully carried out in both alcohols and water.
- Safavi, Afsaneh,Iranpoor, Nasser,Fotuhi, Lida
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p. 2591 - 2594
(2007/10/03)
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- Highly efficient, regio- and stereoselective alcoholysis of epoxides catalyzed with iron(III) chloride
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An efficient, catalytic, simple and mild method for the conversion of epoxides into their corresponding β-alkoxy alcohols was performed in primary, secondary and tertiary alcohols and in the presence of catalytic amounts of ferric chloride. The β-alkoxy alcohols were obtained with high stereo- and regioselectivity and in good to excellent yields.
- Iranpoor,Salehi
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p. 1152 - 1154
(2007/10/02)
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- Tris[Trinitrato Ce(IV)]paraperiodate, an efficient heterogeneous catalyst for alcoholysis, acetolysis and hydrolysis of epoxides
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Tristrinitrato [Ce(IV)]paraperiodate (TTCPP) catalyses ring opening of epoxides in alcohols and water stereo- and regioselectively and under heterogeneous conditions to produce the corresponding β-alkoxy alcohols and 1,2 diols respectively in good to high yields. In acetic acid, ring opening and dimerization of epoxides occurs with this catalyst to produce the corresponding succinic acid derivatives in high yields.
- Iranpoor,Zardaloo
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p. 1959 - 1969
(2007/10/02)
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- Liquid-phase fluorination
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This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
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- Liquid-phase fluorination
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This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
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- Liquid phase fluorination
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This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
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- Investigations on local anaesthetics, IC: Syntheses and local anaesthetic properties of alkoxyphenylcarbamates
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Within the framework of studying the influence of alterations of the connecting chain in the group of local anaesthetics a series of 24 compounds of 1-propoxymethyl-2-(1-pyrrolidinyl), 2-(1-piperidino)-, and 2-(1-perhydroazepinyl)-ethyl esters of o- and m-alkoxyphenylcarbamic acid were prepared. Studied compounds show a high index of relative local anaesthetic activityas compared to the standards cocaine and procaine, at a relatively low acute toxicity.
- Buciova,Csollei,Racanska,Svec
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p. 393 - 396
(2007/10/02)
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- 2,3-Dichloro-5,6-dicyano-p-benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxides
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Ring-opening reactions of epoxides with catalytic amounts of 2,3- Dichloro-5,6-Dicyano-p-Benzoquinone (DDQ) are performed with high regioselectivity under neutral conditions, in primary, secondary and tertiary alcohols as solvents and nucleophiles. The corresponding β- alkoxy alcohols were obtained in excellent yields.
- Iranpoor,Mohammadpour Baltork
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p. 735 - 738
(2007/10/02)
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- Mild, Efficient and Selective Opening of Epoxides with Alcohols Catalyzed by Ceric(IV) Ammonium Nitrate
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Commercially available Ceric(IV) Ammonium Nitrate (CAN) catalyzes nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols under mild conditions.The corresponding β-alkoxy-alcohols were obtained with high regio and stereoselectivity in high yields.
- Iranpoor, N.,Baltork, I. Mohammadpour
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p. 2789 - 2797
(2007/10/02)
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